Dirhodium(II)-Catalyzed C-H Amination Reaction of (S)-3-(tert-Butyldimethylsilyloxy)-2-methylpropyl Carbamate: A Facile Preparation of Optically Active Monoprotected 2-Amino-2-methyl-1,3-propanediol

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  • Yakura Takayuki
    Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama
  • Yoshimoto Yuya
    Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama
  • Ishida Chisaki
    Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama

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  • Dirhodium(2)-catalyzed C-H amination reaction of (S)-3-(tert-butyldimethylsilyloxy)-2-methylpropyl carbamate: a facile preparation of optically active monoprotected 2-amino-2-methyl-1,3-propanediol

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Dirhodium(II)-catalyzed C–H amination reaction of (S)-3-(tert-butyldimethylsilyloxy)-2-methylpropyl carbamate, which was easily prepared from methyl (S)-2-methyl-3-hydroxypropanoate, proceeded more smoothly than those of their 2-(methoxycarbonyl)propyl derivative to give the corresponding oxazolidinone in excellent yield. The resulting oxazolidinone was converted efficiently into both (R)-monoprotected and (S)-monoprotected 2-amino-2-methyl-1,3-propanediols.

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